C7870

Chalcone 4 hydrate

≥98% (HPLC)

• Synonym(s): (E)-1-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one hydrate
• Empirical Formula (Hill Notation): C₁₆H₁₃ClO₃ · xH₂O
• CAS Number: 1202866-96-3
• Molecular Weight: 288.73 (anhydrous basis)
• MDL number: MFCD12912407
• UNSPSC Code: 51111800
• PubChem Substance ID: 329775154
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: solid
• storage condition: protect from light
• color: yellow
• solubility: DMSO: >20 mg/mL
• storage temp.: −20°C
• SMILES string: O.COc1cc(ccc1O)\C=C\C(=O)c2ccc(Cl)cc2
• InChI: 1S/C16H13ClO3.H2O/c1-20-16-10-11(3-9-15(16)19)2-8-14(18)12-4-6-13(17)7-5-12;/h2-10,19H,1H3;1H2/b8-2+;
• InChI key: PXVQKTVKTBMRIW-VOKCZWNHSA-N

Description

Biochem/physiol Actions

Chalcone 4 is a potent, selective inhibitor of the chemokine CXCL12 via direct binding. It is also a small molecule anti-ligand (or neutraligand) of CXCR4 and CXCR7. The chemokine CXCL12 (stromal cell-derived factor-1) and its receptors play pivotal roles in inflammatory responses, normal vascular and neuronal development, as well as in infectious diseases and cancer. Chalcone 4 binds to and activates the chemokine receptors CXCR4 and CXCR7 and stimulates a rapid receptor-mediated intracellular calcium mobilization and signaling through a Pertussis toxin sensitive Gi protein. Chalcone 4 potently and selectively inhibits CXCL12 binding to CXCR4 and CXCR7, and consequent CXCL12-evoked calcium cellular responses. Chalcone 4 binds to the chemokine CXCL12, but not to its receptors.

Features and Benefits

This compound is featured on the Chemokine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.